JP2008239535A - ジヒドロキシベンゼン誘導体の連続式製造方法 - Google Patents
ジヒドロキシベンゼン誘導体の連続式製造方法 Download PDFInfo
- Publication number
- JP2008239535A JP2008239535A JP2007081070A JP2007081070A JP2008239535A JP 2008239535 A JP2008239535 A JP 2008239535A JP 2007081070 A JP2007081070 A JP 2007081070A JP 2007081070 A JP2007081070 A JP 2007081070A JP 2008239535 A JP2008239535 A JP 2008239535A
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- hydroxyphenyl
- ester
- compound represented
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000005205 dihydroxybenzenes Chemical class 0.000 title abstract description 7
- 238000011437 continuous method Methods 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 43
- -1 carboxylic acid halide Chemical class 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000003960 organic solvent Substances 0.000 claims abstract description 22
- 238000005886 esterification reaction Methods 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 150000007514 bases Chemical class 0.000 claims abstract description 6
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 abstract description 16
- 229960001755 resorcinol Drugs 0.000 abstract description 15
- 238000000354 decomposition reaction Methods 0.000 abstract description 12
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract description 6
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 description 29
- 230000008025 crystallization Effects 0.000 description 29
- 238000003756 stirring Methods 0.000 description 15
- 239000007788 liquid Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 238000001914 filtration Methods 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- AWNCOSZGPLLXNC-UHFFFAOYSA-N bis(3-hydroxyphenyl) hexanedioate Chemical compound OC1=CC=CC(OC(=O)CCCCC(=O)OC=2C=C(O)C=CC=2)=C1 AWNCOSZGPLLXNC-UHFFFAOYSA-N 0.000 description 11
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- 239000002245 particle Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000012779 reinforcing material Substances 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 229920002601 oligoester Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
- PTZHISGNBGKPGG-UHFFFAOYSA-N bis(3-hydroxyphenyl) decanedioate Chemical compound OC1=CC=CC(OC(=O)CCCCCCCCC(=O)OC=2C=C(O)C=CC=2)=C1 PTZHISGNBGKPGG-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- DXVYLFHTJZWTRF-UHFFFAOYSA-N Ethyl isobutyl ketone Chemical compound CCC(=O)CC(C)C DXVYLFHTJZWTRF-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- YAZXITQPRUBWGP-UHFFFAOYSA-N benzene-1,3-dicarbonyl bromide Chemical compound BrC(=O)C1=CC=CC(C(Br)=O)=C1 YAZXITQPRUBWGP-UHFFFAOYSA-N 0.000 description 2
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 2
- PIVFDRVXTFJSIW-UHFFFAOYSA-N benzene-1,4-dicarbonyl bromide Chemical compound BrC(=O)C1=CC=C(C(Br)=O)C=C1 PIVFDRVXTFJSIW-UHFFFAOYSA-N 0.000 description 2
- CTTXVICEIPUARX-UHFFFAOYSA-N bis(2-hydroxyphenyl) cyclohexane-1,1-dicarboxylate Chemical compound OC1=CC=CC=C1OC(=O)C1(C(=O)OC=2C(=CC=CC=2)O)CCCCC1 CTTXVICEIPUARX-UHFFFAOYSA-N 0.000 description 2
- VYXZOVLCVHPKPH-FPLPWBNLSA-N bis(3-hydroxyphenyl) (z)-but-2-enedioate Chemical compound OC1=CC=CC(OC(=O)\C=C/C(=O)OC=2C=C(O)C=CC=2)=C1 VYXZOVLCVHPKPH-FPLPWBNLSA-N 0.000 description 2
- PARDGMZERLVHBY-UHFFFAOYSA-N bis(3-hydroxyphenyl) 2,3-dihydroxybutanedioate Chemical compound C=1C=CC(O)=CC=1OC(=O)C(O)C(O)C(=O)OC1=CC=CC(O)=C1 PARDGMZERLVHBY-UHFFFAOYSA-N 0.000 description 2
- ZBXMZDHSINDMAF-UHFFFAOYSA-N bis(3-hydroxyphenyl) 2-methylidenebutanedioate Chemical compound OC1=CC=CC(OC(=O)CC(=C)C(=O)OC=2C=C(O)C=CC=2)=C1 ZBXMZDHSINDMAF-UHFFFAOYSA-N 0.000 description 2
- RNZMAGAKJWUTEF-UHFFFAOYSA-N bis(3-hydroxyphenyl) butanedioate Chemical compound OC1=CC=CC(OC(=O)CCC(=O)OC=2C=C(O)C=CC=2)=C1 RNZMAGAKJWUTEF-UHFFFAOYSA-N 0.000 description 2
- DDPHMTWWRIJAQB-UHFFFAOYSA-N bis(3-hydroxyphenyl) nonanedioate Chemical compound OC1=CC=CC(OC(=O)CCCCCCCC(=O)OC=2C=C(O)C=CC=2)=C1 DDPHMTWWRIJAQB-UHFFFAOYSA-N 0.000 description 2
- PBTOGQAXCLGAJA-UHFFFAOYSA-N bis(3-hydroxyphenyl) propanedioate Chemical compound OC1=CC=CC(OC(=O)CC(=O)OC=2C=C(O)C=CC=2)=C1 PBTOGQAXCLGAJA-UHFFFAOYSA-N 0.000 description 2
- 239000010951 brass Substances 0.000 description 2
- YVXPOZFNECJRIC-UHFFFAOYSA-N butanedioyl dibromide Chemical compound BrC(=O)CCC(Br)=O YVXPOZFNECJRIC-UHFFFAOYSA-N 0.000 description 2
- IRXBNHGNHKNOJI-UHFFFAOYSA-N butanedioyl dichloride Chemical compound ClC(=O)CCC(Cl)=O IRXBNHGNHKNOJI-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- YQAGVUODRGLPSR-UHFFFAOYSA-N decanedioyl dibromide Chemical compound BrC(=O)CCCCCCCCC(Br)=O YQAGVUODRGLPSR-UHFFFAOYSA-N 0.000 description 2
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010981 drying operation Methods 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- UJGPNLWJDSIACI-UHFFFAOYSA-N hexanedioyl dibromide Chemical compound BrC(=O)CCCCC(Br)=O UJGPNLWJDSIACI-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- HGEVGSTXQGZPCL-UHFFFAOYSA-N nonanedioyl dichloride Chemical compound ClC(=O)CCCCCCCC(Cl)=O HGEVGSTXQGZPCL-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- GKIVTXLMSMDQJI-UHFFFAOYSA-N propanedioyl dibromide Chemical compound BrC(=O)CC(Br)=O GKIVTXLMSMDQJI-UHFFFAOYSA-N 0.000 description 2
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- BQYHNFVOXGETHX-ZROIWOOFSA-N (Z)-2-[bis(3-hydroxyphenyl)methyl]but-2-enedioic acid Chemical compound C=1C=CC(O)=CC=1C(/C(=C/C(=O)O)C(O)=O)C1=CC=CC(O)=C1 BQYHNFVOXGETHX-ZROIWOOFSA-N 0.000 description 1
- XGSSMJZGYVOGEM-OWOJBTEDSA-N (e)-but-2-enedioyl dibromide Chemical compound BrC(=O)\C=C\C(Br)=O XGSSMJZGYVOGEM-OWOJBTEDSA-N 0.000 description 1
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 description 1
- XGSSMJZGYVOGEM-UPHRSURJSA-N (z)-but-2-enedioyl dibromide Chemical compound BrC(=O)\C=C/C(Br)=O XGSSMJZGYVOGEM-UPHRSURJSA-N 0.000 description 1
- ZLYYJUJDFKGVKB-UPHRSURJSA-N (z)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C/C(Cl)=O ZLYYJUJDFKGVKB-UPHRSURJSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- YVOMYDHIQVMMTA-UHFFFAOYSA-N 3-Hydroxyadipic acid Chemical compound OC(=O)CC(O)CCC(O)=O YVOMYDHIQVMMTA-UHFFFAOYSA-N 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- NPWUTXQBQANLOL-UHFFFAOYSA-N 4-(2-hydroxyphenoxy)carbonylbenzoic acid Chemical compound OC1=C(C=CC=C1)OC(C1=CC=C(C(=O)O)C=C1)=O NPWUTXQBQANLOL-UHFFFAOYSA-N 0.000 description 1
- ZMAIUFMLHRGWKO-UHFFFAOYSA-N 6-(3-hydroxyphenoxy)-6-oxohexanoic acid Chemical compound OC(=O)CCCCC(=O)OC1=CC=CC(O)=C1 ZMAIUFMLHRGWKO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- NXTGSGDQNSIULG-UHFFFAOYSA-N C(CCCCCCCCCCC)(C(=O)Br)C(=O)Br Chemical compound C(CCCCCCCCCCC)(C(=O)Br)C(=O)Br NXTGSGDQNSIULG-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KVBYPTUGEKVEIJ-UHFFFAOYSA-N benzene-1,3-diol;formaldehyde Chemical compound O=C.OC1=CC=CC(O)=C1 KVBYPTUGEKVEIJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- NXYCLLLUFNEYFP-MDZDMXLPSA-N bis(2-hydroxyphenyl) (e)-but-2-enedioate Chemical compound OC1=CC=CC=C1OC(=O)\C=C\C(=O)OC1=CC=CC=C1O NXYCLLLUFNEYFP-MDZDMXLPSA-N 0.000 description 1
- QYYWMKSLNLMTER-KHPPLWFESA-N bis(2-hydroxyphenyl) (z)-2-methylbut-2-enedioate Chemical compound C=1C=CC=C(O)C=1OC(=O)C(/C)=C\C(=O)OC1=CC=CC=C1O QYYWMKSLNLMTER-KHPPLWFESA-N 0.000 description 1
- VHHMAFOBINYROX-UHFFFAOYSA-N bis(2-hydroxyphenyl) 2,3-dihydroxybutanedioate Chemical compound C=1C=CC=C(O)C=1OC(=O)C(O)C(O)C(=O)OC1=CC=CC=C1O VHHMAFOBINYROX-UHFFFAOYSA-N 0.000 description 1
- AKFTZOYVMJSBIR-UHFFFAOYSA-N bis(2-hydroxyphenyl) 2-methylidenebutanedioate Chemical compound OC1=CC=CC=C1OC(=O)CC(=C)C(=O)OC1=CC=CC=C1O AKFTZOYVMJSBIR-UHFFFAOYSA-N 0.000 description 1
- YYVGWSLPUGIRKE-UHFFFAOYSA-N bis(2-hydroxyphenyl) benzene-1,3-dicarboxylate Chemical compound OC1=CC=CC=C1OC(=O)C1=CC=CC(C(=O)OC=2C(=CC=CC=2)O)=C1 YYVGWSLPUGIRKE-UHFFFAOYSA-N 0.000 description 1
- ORIQNPXYTVKNSZ-UHFFFAOYSA-N bis(2-hydroxyphenyl) butanedioate Chemical compound OC1=CC=CC=C1OC(=O)CCC(=O)OC1=CC=CC=C1O ORIQNPXYTVKNSZ-UHFFFAOYSA-N 0.000 description 1
- HCXCXCNLCOKRTN-UHFFFAOYSA-N bis(2-hydroxyphenyl) decanedioate Chemical compound OC1=CC=CC=C1OC(=O)CCCCCCCCC(=O)OC1=CC=CC=C1O HCXCXCNLCOKRTN-UHFFFAOYSA-N 0.000 description 1
- CJBIXNCYSWCCKB-UHFFFAOYSA-N bis(2-hydroxyphenyl) nonanedioate Chemical compound OC1=CC=CC=C1OC(=O)CCCCCCCC(=O)OC1=CC=CC=C1O CJBIXNCYSWCCKB-UHFFFAOYSA-N 0.000 description 1
- SNJIXFHHUCNLML-UHFFFAOYSA-N bis(2-hydroxyphenyl) propanedioate Chemical compound OC1=CC=CC=C1OC(=O)CC(=O)OC1=CC=CC=C1O SNJIXFHHUCNLML-UHFFFAOYSA-N 0.000 description 1
- VYXZOVLCVHPKPH-BQYQJAHWSA-N bis(3-hydroxyphenyl) (e)-but-2-enedioate Chemical compound OC1=CC=CC(OC(=O)\C=C\C(=O)OC=2C=C(O)C=CC=2)=C1 VYXZOVLCVHPKPH-BQYQJAHWSA-N 0.000 description 1
- OJUVMPCXMHEPAO-FLIBITNWSA-N bis(3-hydroxyphenyl) (z)-2-methylbut-2-enedioate Chemical compound C=1C=CC(O)=CC=1OC(=O)C(/C)=C\C(=O)OC1=CC=CC(O)=C1 OJUVMPCXMHEPAO-FLIBITNWSA-N 0.000 description 1
- WVTQWTYMYFZBDC-UHFFFAOYSA-N bis(3-hydroxyphenyl) benzene-1,3-dicarboxylate Chemical compound OC1=CC=CC(OC(=O)C=2C=C(C=CC=2)C(=O)OC=2C=C(O)C=CC=2)=C1 WVTQWTYMYFZBDC-UHFFFAOYSA-N 0.000 description 1
- GXEVFESZEWKRAP-UHFFFAOYSA-N bis(3-hydroxyphenyl) benzene-1,4-dicarboxylate Chemical compound OC1=CC=CC(OC(=O)C=2C=CC(=CC=2)C(=O)OC=2C=C(O)C=CC=2)=C1 GXEVFESZEWKRAP-UHFFFAOYSA-N 0.000 description 1
- WECOISGMNJGLPF-UHFFFAOYSA-N bis(3-hydroxyphenyl) cyclohexane-1,1-dicarboxylate Chemical compound OC1=CC=CC(OC(=O)C2(CCCCC2)C(=O)OC=2C=C(O)C=CC=2)=C1 WECOISGMNJGLPF-UHFFFAOYSA-N 0.000 description 1
- WRCIZOYVXYPMTF-MDZDMXLPSA-N bis(4-hydroxyphenyl) (e)-but-2-enedioate Chemical compound C1=CC(O)=CC=C1OC(=O)\C=C\C(=O)OC1=CC=C(O)C=C1 WRCIZOYVXYPMTF-MDZDMXLPSA-N 0.000 description 1
- KOPZFEYNQWRUES-KHPPLWFESA-N bis(4-hydroxyphenyl) (z)-2-methylbut-2-enedioate Chemical compound C=1C=C(O)C=CC=1OC(=O)C(/C)=C\C(=O)OC1=CC=C(O)C=C1 KOPZFEYNQWRUES-KHPPLWFESA-N 0.000 description 1
- WRCIZOYVXYPMTF-KTKRTIGZSA-N bis(4-hydroxyphenyl) (z)-but-2-enedioate Chemical compound C1=CC(O)=CC=C1OC(=O)\C=C/C(=O)OC1=CC=C(O)C=C1 WRCIZOYVXYPMTF-KTKRTIGZSA-N 0.000 description 1
- HUBKPLIESUBWHE-UHFFFAOYSA-N bis(4-hydroxyphenyl) 2,3-dihydroxybutanedioate Chemical compound C=1C=C(O)C=CC=1OC(=O)C(O)C(O)C(=O)OC1=CC=C(O)C=C1 HUBKPLIESUBWHE-UHFFFAOYSA-N 0.000 description 1
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- MLWDFHBGADSHPT-UHFFFAOYSA-N bis(4-hydroxyphenyl) benzene-1,3-dicarboxylate Chemical compound C1=CC(O)=CC=C1OC(=O)C1=CC=CC(C(=O)OC=2C=CC(O)=CC=2)=C1 MLWDFHBGADSHPT-UHFFFAOYSA-N 0.000 description 1
- PZKYPEIOGNUSOC-UHFFFAOYSA-N bis(4-hydroxyphenyl) benzene-1,4-dicarboxylate Chemical compound C1=CC(O)=CC=C1OC(=O)C1=CC=C(C(=O)OC=2C=CC(O)=CC=2)C=C1 PZKYPEIOGNUSOC-UHFFFAOYSA-N 0.000 description 1
- RTKIVAUYAAOUNG-UHFFFAOYSA-N bis(4-hydroxyphenyl) butanedioate Chemical compound C1=CC(O)=CC=C1OC(=O)CCC(=O)OC1=CC=C(O)C=C1 RTKIVAUYAAOUNG-UHFFFAOYSA-N 0.000 description 1
- IYHICXNYLUTBFZ-UHFFFAOYSA-N bis(4-hydroxyphenyl) cyclohexane-1,1-dicarboxylate Chemical compound C1=CC(O)=CC=C1OC(=O)C1(C(=O)OC=2C=CC(O)=CC=2)CCCCC1 IYHICXNYLUTBFZ-UHFFFAOYSA-N 0.000 description 1
- RGHMDKSWCOFSMY-UHFFFAOYSA-N bis(4-hydroxyphenyl) decanedioate Chemical compound C1=CC(O)=CC=C1OC(=O)CCCCCCCCC(=O)OC1=CC=C(O)C=C1 RGHMDKSWCOFSMY-UHFFFAOYSA-N 0.000 description 1
- JMOWLADXOKKZQZ-UHFFFAOYSA-N bis(4-hydroxyphenyl) hexanedioate Chemical compound C1=CC(O)=CC=C1OC(=O)CCCCC(=O)OC1=CC=C(O)C=C1 JMOWLADXOKKZQZ-UHFFFAOYSA-N 0.000 description 1
- UEAYJLUKOWUNGO-UHFFFAOYSA-N bis(4-hydroxyphenyl) nonanedioate Chemical compound C1=CC(O)=CC=C1OC(=O)CCCCCCCC(=O)OC1=CC=C(O)C=C1 UEAYJLUKOWUNGO-UHFFFAOYSA-N 0.000 description 1
- QXJKPARWFMSDRC-UHFFFAOYSA-N bis(4-hydroxyphenyl) propanedioate Chemical compound C1=CC(O)=CC=C1OC(=O)CC(=O)OC1=CC=C(O)C=C1 QXJKPARWFMSDRC-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- BXLBOLOUCITZFA-UHFFFAOYSA-N cyclohex-2-ene-1,1-dicarbonyl bromide Chemical compound BrC(=O)C1(C(Br)=O)CCCC=C1 BXLBOLOUCITZFA-UHFFFAOYSA-N 0.000 description 1
- OANFVMFCLUSQJY-UHFFFAOYSA-N cyclohex-2-ene-1,1-dicarbonyl chloride Chemical compound ClC(=O)C1(C(Cl)=O)CCCC=C1 OANFVMFCLUSQJY-UHFFFAOYSA-N 0.000 description 1
- BTLPDWRKFKDZIH-UHFFFAOYSA-N cyclohexane-1,1-dicarbonyl bromide Chemical compound BrC(=O)C1(C(Br)=O)CCCCC1 BTLPDWRKFKDZIH-UHFFFAOYSA-N 0.000 description 1
- MLCGVCXKDYTMRG-UHFFFAOYSA-N cyclohexane-1,1-dicarbonyl chloride Chemical compound ClC(=O)C1(C(Cl)=O)CCCCC1 MLCGVCXKDYTMRG-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 125000005469 ethylenyl group Chemical group 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000002905 metal composite material Substances 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- HCIQVHYVJXUCPJ-UHFFFAOYSA-N nonanedioyl dibromide Chemical compound BrC(=O)CCCCCCCC(Br)=O HCIQVHYVJXUCPJ-UHFFFAOYSA-N 0.000 description 1
- FVENDMFTYXWGLT-UHFFFAOYSA-N octanedioyl dibromide Chemical compound BrC(=O)CCCCCCC(Br)=O FVENDMFTYXWGLT-UHFFFAOYSA-N 0.000 description 1
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- YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
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- 238000004062 sedimentation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005760 substituted naphthylene group Chemical group 0.000 description 1
- 125000005650 substituted phenylene group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- DBZWFSYEKKZLNS-UHFFFAOYSA-N tetradecanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCCCCCC(Cl)=O DBZWFSYEKKZLNS-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
【解決手段】(a)実質的に水と不混和性の有機溶媒にジヒドロキシベンゼンを溶解または懸濁し、塩基性化合物で部分中和する工程(b)続いてカルボン酸ハライドを滴下装入しつつ反応させる工程(エステル化反応工程)(c)エステル化反応時の温度よりも高い温度で熱処理する工程(オリゴマー分解工程)(d)前記(c)で得られた混合物を水と接触させて連続的に晶析し生成物を析出させる工程からなる事を特徴とするジヒドロキシベンゼン誘導体の製造方法を提供する。
【選択図】なし
Description
[1](a)実質的に水と不混和性の有機溶媒に一般式(1)で表される化合物
(b)続いて一般式(2)で表されるカルボン酸ハライド
を滴下装入しつつ反応させる工程、
(c)エステル化反応時の温度よりも高い温度で熱処理する工程、
(d)前記(c)で得られた混合物を水と接触させて連続的に晶析し生成物を析出させる工程
からなる事を特徴とする一般式(3)で表される化合物の製造方法である。
[2]一般式(3)で表される化合物が、下記一般式(4)
で表される化合物である[1]に記載の製造方法。
[3]一般式(4)で表される化合物中に、下記一般式(5)で表される化合物が0〜30%含まれる事を特徴とする[1]〜[2]のいずれかに記載の製造方法。
本発明に使用される一般式(1)で表される化合物としては、カテコール、レゾルシンおよびハイドロキノンが挙げられる。これらの中ではレゾルシンが好ましい。
1)脱MIBKマスの製造例
反応器(撹拌槽、内容積500L)にて、レゾルシン(以下、RSと略)176kgをメチルイソブチルケトン(以下、MIBKと略)176kgに溶解し、30.6質量%のNaOH水溶液38.7kgを添加して部分中和した。その後、11℃まで冷却し、10〜15℃を維持しながら塩化アジポイル(以下、ADCと略)27.8kg(純度95.6%)を6時間かけて滴下しつつエステル化反応を行い、同温度で1時間熟成を行った。
晶析機(撹拌槽、内容積230L)に5℃の冷水121kgを装入し、撹拌を行った。得られた脱MIBKマス(120℃)27.7kgを、流量7.2kg/hにて晶析機に供給して回分式の晶析操作を行い、アジピン酸ビス(3−ヒドロキシフェニル)エステルのスラリーを得た。次いで、冷水(5℃)を流量31.4kg/h、脱MIBKマス(120℃)を流量7.2kg/hにて各々連続的に供給し、連続晶析操作を実施した。撹拌槽の滞留液量は滞留時間が3.3時間となるように設定した。連続運転中、晶析機の内温は13〜15℃に維持された。
晶析機から連続的に排出されるアジピン酸ビス(3−ヒドロキシフェニル)エステルのスラリーは、一旦、中継槽に保管後、加圧濾過器(濾過面積0.2m2)を用いて固液分離操作を行った。濾過速度(濾過面積[m2]当たりの濾液平均流量[kg/h])は、25,000kg/h・m2を示し、極めて良好であった。濾過後、さらに水でリンス操作を行い、含水率38%のウェットケーキを得た。得られたウェットケーキを光学顕微鏡で確認した結果、粒径700〜1000μmを有する真球状粒子であることが分かった。
濾過工程で得たウェットケーキを回転撹拌式乾燥機(コニカル乾燥機)に装入し、減圧下(40mmHg前後)にてジャケット温度70℃で乾燥操作を行った。約20時間後、アジピン酸ビス(3−ヒドロキシフェニル)エステル中の水分は0.2質量%となり、乾燥操作を終了した。アジピン酸ビス(3−ヒドロキシフェニル)エステルの収量は、脱MIBKマス供給量100kg当たり、アジピン酸ビス(3−ヒドロキシフェニル)エステルの乾燥品として26kgであった(粗収率88%)。
1)バッチ晶析工程
晶析機(撹拌槽、内容積1000L)に冷水(5℃)417kgを装入し、撹拌を行った。実施例1と同様の操作を繰り返し、得られた脱MIBKマス(120℃)101kgを、30分かけて晶析機に供給し、回分式の晶析操作を行ってアジピン酸ビス(3−ヒドロキシフェニル)エステルのスラリーを得た。晶析過程で、内温は5℃から14℃に上昇した。
晶析機から連続的に排出されるアジピン酸ビス(3−ヒドロキシフェニル)エステルのスラリーは、一旦、中継槽に保管後、加圧濾過器(濾過面積0.2m2)を用いて固液分離操作を行った。濾過速度(濾過面積[m2]当たりの濾液平均流量[kg/h])は、7,000kg/h・m2を示した。濾過後、さらに水でリンス操作を行い、含水率51%のウェットケーキを得た。得られたウェットケーキを光学顕微鏡で確認した結果、粒径10μmオーダーの不定形粒子であることが分かった。
実施例1と同様の操作を繰り返して製造した脱MIBKマスを用い、以下の工程を実施した。
1)連続晶析工程
晶析機(撹拌槽、内容積230L)に5℃の冷水117kgを装入し、撹拌を行った。実施例1と同様の操作を繰り返し、得られた脱MIBKマス(120℃)31.3kgを、流量19.0kg/hにて晶析機に供給して回分式の晶析操作を行い、アジピン酸ビス(3−ヒドロキシフェニル)エステルのスラリーを得た。次いで、冷水(5℃)を流量71.1kg/h、脱MIBKマス(120℃)を流量19.0kg/hにて各々連続的に供給し、連続晶析操作を実施した。撹拌槽の滞留液量は滞留時間が1.5時間となるように設定した。連続運転中、撹拌槽の内温は13〜15℃に維持された。
晶析機から連続的に排出されるアジピン酸ビス(3−ヒドロキシフェニル)エステルのスラリーは、一旦、中継槽に保管後、連続式遠心分離機に流量1.1m3/hで供給した。遠心分離機ではアジピン酸ビス(3−ヒドロキシフェニル)エステルの結晶と濾液が、連続的に分離され、含水率20%のウェットケーキを得た。
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Cited By (2)
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JP5362703B2 (ja) * | 2008-03-19 | 2013-12-11 | 三井化学株式会社 | ジヒドロキシベンゼン誘導体の製造方法 |
EP2960278A1 (de) * | 2014-06-23 | 2015-12-30 | LANXESS Deutschland GmbH | Haftsysteme für Kautschukmischungen |
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JPS5287113A (en) * | 1976-01-13 | 1977-07-20 | Mitsubishi Gas Chem Co Inc | Production of ester |
JPS58108527A (ja) * | 1981-12-10 | 1983-06-28 | チバ・ガイギ−・ア−ゲ− | 写真材料 |
JPH07118621A (ja) * | 1993-10-19 | 1995-05-09 | Sumitomo Chem Co Ltd | 接着剤およびそれのゴムへの適用 |
JPH11158140A (ja) * | 1997-11-26 | 1999-06-15 | Sumitomo Chem Co Ltd | メチオニンの製造方法 |
WO2005087704A1 (ja) * | 2004-03-12 | 2005-09-22 | Mitsui Chemicals, Inc. | 化合物及びそれを含む組成物 |
JP2008127286A (ja) * | 2006-11-16 | 2008-06-05 | Mitsui Chemicals Inc | ジヒドロキシベンゼン誘導体の製造方法 |
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2007
- 2007-03-27 JP JP2007081070A patent/JP5236887B2/ja active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS5287113A (en) * | 1976-01-13 | 1977-07-20 | Mitsubishi Gas Chem Co Inc | Production of ester |
JPS58108527A (ja) * | 1981-12-10 | 1983-06-28 | チバ・ガイギ−・ア−ゲ− | 写真材料 |
JPH07118621A (ja) * | 1993-10-19 | 1995-05-09 | Sumitomo Chem Co Ltd | 接着剤およびそれのゴムへの適用 |
JPH11158140A (ja) * | 1997-11-26 | 1999-06-15 | Sumitomo Chem Co Ltd | メチオニンの製造方法 |
WO2005087704A1 (ja) * | 2004-03-12 | 2005-09-22 | Mitsui Chemicals, Inc. | 化合物及びそれを含む組成物 |
JP2008127286A (ja) * | 2006-11-16 | 2008-06-05 | Mitsui Chemicals Inc | ジヒドロキシベンゼン誘導体の製造方法 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP5362703B2 (ja) * | 2008-03-19 | 2013-12-11 | 三井化学株式会社 | ジヒドロキシベンゼン誘導体の製造方法 |
EP2960278A1 (de) * | 2014-06-23 | 2015-12-30 | LANXESS Deutschland GmbH | Haftsysteme für Kautschukmischungen |
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